4-(Trifluoromethyl)thiobenzamide Chemical Properties

Melting point:

136-137 °C

Boiling point:

246.0±50.0 °C(Predicted)

Density 

1.372±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

pka

12.04±0.29(Predicted)

form 

powder to crystal

color 

Light yellow to Yellow to Green

Sensitive 

Stench

BRN 

4672885

InChI

InChI=1S/C8H6F3NS/c9-8(10,11)6-3-1-5(2-4-6)7(12)13/h1-4H,(H2,12,13)

InChIKey

IPRFNMJROWWFBH-UHFFFAOYSA-N

SMILES

C1(C(N)=S)=CC=C(C(F)(F)F)C=C1

CAS DataBase Reference

72505-21-6(CAS DataBase Reference)

NIST Chemistry Reference

4-(Trifluoromethyl)thiobenzamide(72505-21-6)

Safety Information

Hazard Codes 

Xn,Xi,T

Risk Statements 

20/21/22-36/37/38

Safety Statements 

36/37/39-26-22-36

RIDADR 

2811

Hazard Note 

Irritant/Stench

HazardClass 

6.1

PackingGroup 

III

HS Code 

29309090

MSDS

• Language:English Provider:4-(Trifluoromethyl)thiobenzamide
• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-(Trifluoromethyl)thiobenzamide Usage And Synthesis

Chemical Properties

Yellow crystalline powder

Synthesis

The general procedure for the synthesis of 4-(trifluoromethyl)thiobenzamide from 4-trifluoromethylbenzonitrile was as follows: 500 mg (2.92 mmol) of 4-trifluoromethylbenzonitrile was reacted with 702 mg (8.7 mmol) of sodium thiohydride for 3 hr at 60 °C. Ethanol was used as a solvent during the reaction, and the ethanol was removed by distillation after the reaction was completed. Subsequently, ethyl acetate was added to the reaction mixture and the resulting solution was washed with water. The organic layer was dried with anhydrous magnesium sulfate and then the solvent was removed by distillation. The residue was purified by column chromatography to give 517 mg (95% yield) of 4-(trifluoromethyl)thiobenzamide. The product could be used in the next step of the reaction without further purification. Mass spectrometry (EI) showed a molecular ion peak of 152 (M++1).

References

[1] Journal of Medicinal Chemistry, 2014, vol. 57, # 8, p. 3213 - 3222
[2] Patent: WO2005/40127, 2005, A1. Location in patent: Page/Page column 100-101
[3] Journal of Fluorine Chemistry, 2006, vol. 127, # 1, p. 63 - 67
[4] Patent: WO2004/6922, 2004, A1. Location in patent: Page/Page column 27; 28
[5] RSC Advances, 2018, vol. 8, # 1, p. 170 - 175

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